After years in the staffing industry, I’ve noticed something: We keep making the same sales mistakes. Over and over again.
No matter the company, no matter the economic cycle, we tend to react instead of plan. We chase too many opportunities, assume we know what our customers want, misplace great people in the wrong roles, and measure the wrong things—keeping us busy instead of effective.
And the worst part? These mistakes are expensive. Salespeople are expensive. Time is expensive. Missed opportunities are expensive.
But here’s the good news: If we can recognize these patterns, we can break them.
So let’s talk about the four biggest mistakes we keep making in sales—and what we can do about them.
Mistake #1: We Get the Customer Wrong
This should be the easy part, right? But time and time again, we start with us—our product, our pitch, our process—rather than focusing on who our customer is and what actually matters to them.
If we don’t define our ideal customer, our strategy is unfocused, our messaging is weak, and our win rates drop. We either try to sell to everyone or target the wrong buyers altogether.
How to Fix It:
✔ Get specific. What size companies are we targeting? What industries? Who is the actual decision-maker?
✔ Understand their pain points. What business problems are they trying to solve? How do those problems impact them financially, operationally, and personally?
✔ Align to their buying process. Some customers need a fast, transactional sale. Others require a longer, consultative approach. Are we meeting them where they are?
If we don’t answer these questions upfront, we waste time chasing deals we were never going to win.
Mistake #2: We Put the Right People in the Wrong Roles
Hiring great salespeople isn’t just about finding the right kind of person. Even the best sales reps will fail if their skills don’t align with the job we expect them to do.
I learned this the hard way when I hired 40 salespeople in one year. Some crushed it. Some never should have been hired in the first place. But the biggest loss? The ones who could have succeeded if we had put them in the right roles.
How to Fix It:
✔ Match skills to the job. Not every sales role is the same, and not every salesperson is built for every job.
✔ Distinguish between must-have and nice-to-have qualities. Some traits (like curiosity and resilience) are universal, but others (like negotiation skills or technical expertise) should vary by role.
✔ Hire for the role, not the resume. Don’t assume a top performer in one role will succeed in another.
When we misalign people, they struggle. We think the rep is the problem when really, we set them up to fail.
Mistake #3: We Treat Sales Like an Isolated Department
Too often, companies focus only on new customer acquisition and leave retention and expansion to chance.
Leaders say, “I need to hire a hunter.” But hunters are rare, expensive, and take time to deliver. Meanwhile, we’re leaving money on the table by ignoring the customers we already have.
How to Fix It:
✔ Think beyond acquisition. Revenue doesn’t just come from new deals—it comes from retaining and growing existing accounts.
✔ Align sales with marketing and customer success. Sales doesn’t operate in a vacuum. Marketing should drive awareness and demand. Customer success should play a proactive role in expansion.
✔ Use technology and outsourcing strategically. If a full marketing team isn’t feasible, can you leverage a contractor? Can automation help with lead nurturing?
If we put sales in charge of the entire revenue lifecycle, we set them up to fail. But if we balance acquisition, retention, and expansion, we create a revenue engine that compounds over time.
Mistake #4: We Measure the Wrong Things
Let’s be honest—sales leaders love activit. Calls, emails, LinkedIn invites.. It all feels productive.
But then a quarter goes by, and we’re shocked when revenue doesn’t magically appear.
The truth? Not all activity is created equal. If we’re not tracking what actually drives revenue, we’re just busy instead of effective.
How to Fix It:
✔ Focus on conversion, not activity. Are we getting meetings with the right decision-makers? And are we turning those meetings into business?
✔ Use activity as a diagnostic tool, not a success metric. Calls and emails can tell us what’s working, but they don’t determine success on their own.
✔ Keep it simple. The two things that really matter:
→ Are we getting the right meetings?
→ Are we converting them into revenue?
Breaking the Cycle
We’ve been making these mistakes for years. But we don’t have to keep making them.
The companies that get this right—who deeply understand their customers, align talent properly, build a true revenue team, and measure the right things—grow faster, retain more revenue, and waste far less time.
More deals. Less wasted effort. Fewer expensive mistakes.
Sounds like a better way to sell, doesn’t it?
What about you? What’s the biggest sales mistake you’ve seen (or made)? Drop a comment below—I’d love to hear your thoughts.
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